Head of Sales

About SkillsWave

SkillsWave is on a mission to drive people and businesses forward—building tomorrow’s most valued skills, today. By providing quality learning opportunities that align with organizational needs, we’re helping organizations transform their workforce into a competitive advantage. Our upskilling platform and strategic education partnerships not only propel career and company growth, but also deliver measurable and meaningful ROI for learning. To learn more, visit SkillsWave.com. 

Catch the Wave with Us!

Dive into an exciting role as Head of Sales. Reporting to the President you’ll ride the wave of success in a pivotal executive role in a scaling start up environment, driving the company’s revenue growth, go-to-market execution, and overall commercial success. This individual will own the full sales cycle—from strategy through execution—and will lead, scale, and inspire a high-performing sales organization that consistently delivers against aggressive growth targets.

As a member of the leadership team, the Head of Sales will collaborate cross-functionally with Marketing, Product, Customer Success, People & Culture and Finance to align revenue-generating efforts and ensure that sales strategy and execution are tightly integrated with broader company objectives. The ideal candidate brings deep experience in enterprise SaaS or technology sales, a data-driven mindset, and a proven track record of building and leading successful sales teams at scale.

In addition to owning new customer acquisition, this leader will be responsible for expanding existing customer relationships, optimizing sales processes, and leveraging insights to continuously improve performance. They must combine strategic thinking with a hands-on leadership style, fostering a culture of accountability, agility, and customer-first selling.

This is a high-impact, high-visibility role that will shape the company’s commercial engine during a critical period of growth and transformation.

If you're ready to ride the wave of innovation and contribute to something big, this is the role for you!

Your Location, Your Workspace, Your Wave

We are looking for the right person to join our team. This position offers a remote option along with a hybrid option if you are located in the Kitchener/Waterloo area and want to enjoy our amazing space at Catalyst Commons. We can’t wait to welcome exceptional individuals that will bring their skills and passion to our team!

How Will You Make an Impact:

• Drive overall revenue growth through a well-defined, scalable go-to-market strategy.
• Lead the sales organization across new business, customer expansion, and strategic partnerships.
• Develop and implement repeatable sales processes and GTM playbooks.
• Build and manage the full sales funnel, forecast performance, and implement systems for transparency and accountability.
• Cultivate a high-performance team culture, recruiting and coaching top-tier talent.
• Work cross-functionally with Product, Marketing, and Customer Success to align messaging, product positioning, and account targeting.
• Leverage CRM (Hubspot) and the broader sales tech stack to optimize pipeline and performance visibility.
• Actively engage in enterprise-level deals, acting as executive sponsor to key accounts.
• Monitor market trends and competition to inform strategic direction.
• Collaborate with the executive team on pricing, strategic partnerships, and expansion plans.

What You Need to Be Successful:

• 15+ years of B2B and B2C sales experience in the tech sector with 5+ years in executive sales leadership.
• Experience in a SaaS startup or scale-up, particularly in learning, HR tech, or workforce enablement.
• Expertise in sales strategy, forecasting, pipeline management, and performance analytics.
• Proven success growing and leading sales organizations from early-stage to $50M+
• Strong knowledge of the U.S. and Canadian markets, especially selling into HR, L&D, or Operations leaders.
• Deep expertise in consultative selling, enterprise deal management, and team development.
• Demonstrated ability to build structure and momentum in dynamic, fast-paced environments.
• Analytical and operational mindset with strong command of forecasting, KPIs, and sales metrics.
• Highly collaborative, humble, and motivated by shared success.

Your Super Skills and The Wave-Riding Expertise We Need!:

• Expertise in sales strategy, process design, GTM planning, and long-term growth alignment.
• Clear communicator who can align internal stakeholders and inspire external prospects.
• Comfortable closing enterprise deals while building team and process foundations.
• Proven success recruiting, developing, and retaining top-performing sales talent.
• Ability to pivot quickly and make confident decisions under pressure

What You Will Bring to the Team:

• An Enthusiastic Perspective: An independent self-starter, someone who is curious about what and why, is able to solution with empathy for stakeholders, and drive successful change through yourself and leveraging others
• Entrepreneurial Spirit: Demonstrating initiative, creativity, and ownership by proactively identifying opportunities, solving problems, and taking calculated risks to drive innovation and organizational growth
• Customer Obsession: Focused on deeply understanding customer needs and delivering exceptional value.
• Accountability for Results: Takes ownership of outcomes and consistently drives toward measurable goals.
• Growth Mindset: Embraces continuous learning, iteration, and feedback.
• Strategic Thinking: Connects day-to-day execution to long-term business goals and vision.
• Collaboration & Influence: Builds strong relationships across teams and inspires others toward common goals.
• Data-Driven Decision Making: Uses data to inform actions and optimize performance.
• Resilience & Grit: Maintains focus and determination in the face of challenges and change.

Who You Are:

• You Own It: You approach every challenge with the mentality of a surfer tackling a perfect wave—taking full ownership of your work and responsibilities, driving projects forward with confidence and initiative.
• You Learn It: You believe that improvement is key, constantly refining your skills. Growth and learning are always top of mind.
• You Collaborate Assertively: You engage confidently in team discussions, share your expertise, and ensure that everyone is paddling in sync toward success.
• You Work with Velocity and Quality: Whether you’re racing towards the shore or patiently navigating the break, you strike the perfect balance between speed and delivering top-notch results.
• You Care Deeply: You care deeply about your work and the lasting impact it makes—on your team, the company, and beyond.

Surf's Up! Dive Into Our Benefits:

• Competitive Salary
• Vacation and Rest Days
• Health & Wellness
• Retirement Savings Plan
• Professional Development

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Background Check Notice

As part of our hiring process, SkillsWave may conduct a background check to ensure the safety and security of our workplace.

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